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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
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31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

B&B in Westchester

Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (78)
"Clean room beautiful.yards convenient"
The price is AED 234
AED 403 total
includes taxes & fees
6 Oct - 7 Oct
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (610)
"Just a wonderful tranquil oasis in such a large city and busy section of town."
The price is AED 240
AED 429 total
includes taxes & fees
6 Oct - 7 Oct
The Villa Toscana
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (477)
"Loved the shared kitchen access! "
The price is AED 701
AED 823 total
includes taxes & fees
7 Oct - 8 Oct
The Sono Chicago
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (378)
"Absolutely one of the best stays I’ve ever had. "
The price is AED 619
AED 699 total
includes taxes & fees
6 Oct - 7 Oct
Ray's Bucktown B&B
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (185)
"Wonderful staff, beautiful hotel and great breakfast!"
The price is AED 794
AED 897 total
includes taxes & fees
29 Oct - 30 Oct
The Publishing House B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (484)
"The space was neat and clean. The bed was really nice comfortable and the breakfast being available whenever was nice to have! Other guests were not an issue and checkin/checkout was very easy."
The price is AED 418
AED 693 total
includes taxes & fees
15 Oct - 16 Oct
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (252)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (110)
"Great place"
The price is AED 883
AED 1,036 total
includes taxes & fees
27 Oct - 28 Oct
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is AED 962
AED 1,068 total
includes taxes & fees
7 Oct - 8 Oct
Harvey House Bed & Breakfast
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (147)
"Great location. Location was clean and everything was good!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Adorable bed & breakfast in Chicago2222
Pool

Adorable bed & breakfast in Chicago2222

2.0 star property
Adorable bed & breakfast in Chicago2222
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westchester Hotel Reviews

Freehand Chicago

Freehand Chicago

10/10 Excellent
"(Private queen room) the room was small but very comfortable. Everyone was very nice and friendly. Would absolutely stay again. "
jonathan 1-night trip
Posted 5 hours ago
Freehand Chicago

Frequently asked questions

Searching for B&Bs in Westchester?
Whether you're on a family vacation and want a small, cozy place to stay, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. If you're interested in discovering some top attractions, Wrigley Field and Michigan Avenue are worth a stop.
Why consider B&Bs instead of traditional hotels?
With attentive service, opportunities to mingle with other guests, and of course a full breakfast to start the day, B&Bs offer a truly one-of-a-kind environment.
What are the best B&Bs in Westchester?
Here are some well-liked B&Bs in the area: Dorothy's: 7 rooms. 13.6 mi (21.9 km) from the heart of Westchester.House 5863 - Chicago Bed and Breakfast: 7 rooms. 14.7 mi (23.6 km) from the downtown core. Enjoy the designer toiletries and private yard. The Villa Toscana: 9 rooms. Situated 13.6 mi (21.9 km) from the heart of Westchester. The Sono Chicago: 7 rooms. 13 mi (20.9 km) from the heart of downtown. Enjoy the rooftop terrace and fireplace in the lobby. Ray's Bucktown B&B: 11 rooms. Located 11.3 mi (18.2 km) from the core of Westchester. Enjoy the free cooked breakfast and rooftop terrace.
What's the best time of year to book my B&B in Westchester?
When you're planning your getaway to Westchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What is there to do in Westchester?
Travelers enjoy Westchester for its restaurants and shopping. You might also consider a trip to sites like Wrigley Field or Michigan Avenue if you have time to see more of the area.
How can I get to and around Westchester?
You can map out your trip in and around Westchester ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) away from the heart of the city. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to explore around the area, you may want a rental car for your journey.